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From Multiple to Meaningful: Strategy lessons from 1987 to Today

Jun 9, 2025 | Blog

In the mid-1980s, I was about a year into a new position with Merrill Lynch. I was fortunate to have landed there and felt a deep sense of gratitude and responsibility. I worked hard and learned fast, but at the time, I didn’t know much. My father-in-law once put it bluntly, stating that I didn’t know the difference between a …certain substance… and Shineola.

With that humility handed to me, I still enjoyed my position. It was unique, and allowed me to gain a great deal of exposure to many planning concepts and techniques. 

Early in my role,  a new product with huge tax appeal was rolled out. It was marketed heavily, and from a tax standpoint, was very effective.

Inside this product/plan were several custom-designed investment options. A particularly memorable option was called Multiple Strategies. It was pitched as a kind of perfect solution: the growth potential of stocks, the safety of bonds, and a structure that was described as being able to weather any market condition. The perfect foil to volatility. Predictably, most of the money that flowed into this product—probably 90%—was allocated to the Multiple Strategies investment option.

Then came October 19, 1987. Black Monday.

Markets dropped sharply. The S&P 500 fell by 20.47% in a single day, the largest single-day percentage loss in the S&P 500’s history. People in our office sat stunned, helpless as prices tanked.

But what about Multiple Strategies? Did the genius creation save the day? Unfortunately, it fell just as hard. The very thing that was supposed to buffer against risk offered very little protection at all. It did however gain a new nickname in our office: Multiple Tragedies.

That experience stuck with me. I’ve seen more than my share of “can’t miss” ideas since then.

Which brings me to what I love and appreciate about what Greg does for our clients.

My business partner and Topturn co-founder, Greg Stewart, uses and continues to refine a tactical methodology designed to help our clients make headway in volatile markets. Bear in mind, these are clients that often remind us that they “don’t ever want to have to start over again“.

Interestingly, late 2024 set the stage for an example of how this tactical method comes into play. Heading into the end of the year the S&P 500 had gained more than 20%, on the heels of a 20% plus return in 2023. Historically, it is rare for the S&P 500 to produce back-to-back gains of that size, and the indicators Greg follows (designed to help remove emotion from the equation) were showing signs that the market had become overbought.

Greg responded by selectively dialing back our client exposure to stocks, and reallocating across a few safe haven areas, most notably: money market instruments, gold and inflation-protected treasury securities.

Subsequently, when the S&P 500 took a meaningful dip in early 2025, we were buffered to a degree. Not immune, but significantly more insulated than we would have otherwise been.

It’s not magic. It’s not market timing. It’s about paying attention, staying disciplined, and having a thoughtful process for taking risk off the table when indicated.

If you’re reading this and wondering what your current portfolio looks like through that same lens, we can help. We’re offering a complimentary portfolio analysis that is quick, objective, and could offer real insight. No cost, no obligation, just good information.

If you’re interested in the complimentary portfolio analysis, simply fill out the form below and we’ll take care of the rest!

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